CN101768376A - Environment-friendly disperse dye composition - Google Patents

Environment-friendly disperse dye composition Download PDF

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Publication number
CN101768376A
CN101768376A CN200910156640A CN200910156640A CN101768376A CN 101768376 A CN101768376 A CN 101768376A CN 200910156640 A CN200910156640 A CN 200910156640A CN 200910156640 A CN200910156640 A CN 200910156640A CN 101768376 A CN101768376 A CN 101768376A
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alkyl
dye
dye monomer
formula
disperse
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CN101768376B (en
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赵国生
高立江
顾伟娣
陈百龙
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Zhejiang Runtu Co Ltd
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Zhejiang Runtu Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes

Abstract

The invention discloses an environment-friendly disperse dye composition, which comprises the following components by weight percent: 10-75% of dye monomer A as shown in formula (1), 2-35% of dye monomer B as shown in formula (2), 8-50% of dye monomer C as shown in formula (3), and 1-10% of dye monomer D as shown in formula (4). The disperse dye composition can be regulated to obtain colored lights such as black, blue, grey, brown and the like; the obtained dye composition is an environment-friendly dye, and has wide suitable range of the pH value, good pile-on property, strong covering performance, good lifting power, colour yield, levelling property and various fastness, and can greatly improve the utilization rate of the dye and reduce the dye sewage.

Description

A kind of disperse dye composition of environment-friendly type
Technical field
The present invention relates to a kind of environmental-friendly disperse dye composition, be specially adapted to the dyeing and the stamp of terylene and BLENDED FABRIC thereof.
Background technology
In dispersed dye, C.I.Disperse Orange 76# (76# orange) is because of its equalization is good, and fastness is good, and colorant match is good, usually compound with C.I.Disperse Blue 291:1#, C.I.Disperse Violet93#, piece together high-intensity black, the blue serial dispersed dye of system.This is black, not only intensity height but also depth are fabulous for dispersed dye of blue series, and be very extensive in the application of dyeing polyester materials.But owing to the 76# orange can cracking produce harmful arylamine under given conditions, it is irritated that human body is produced, therefore the high strength that has 76# orange dispersed dye black, blue series are classified as the forbidding dyestuff by European Union member countries such as Germany, though black, the blue serial substitute products of many environment-friendly types are arranged on the market, and its depth and lid screening dynamics all do not reach previous level.Seek environment-friendly type, black, the blue serial disperse dye composition of depth, opacifying property all good high strength is that pendulum is badly in need of the difficult problem that solves in face of everybody at present.
Summary of the invention
The invention provides a kind of environmental protection, depth, opacifying property fabulous high strength is disperseed the dye composite of black blue series, this disperse dye composition belongs to intensity height, depth is good, dye yield is high, homogeneity is good high strength disperse dye composition.
A kind of disperse dye composition of environment-friendly type, by weight percentage, mainly form by following component:
10%～75% dye monomer A as the formula (1):
Figure G2009101566400D00011
X wherein 1Be H or CN or NO 2
X 2Be H or halogen, and X 1And X 2Be not H simultaneously;
X 3Be H or C 1～C 4Alkyl or NHCOR 3Or OH; R 3Be C 1～C 4Alkyl;
X 4Be H or OH or OR 4Or R 5OR 6R 4, R 5, R 6Independent separately is C 1～C 4Alkyl;
R 1, R 2Independent separately is H or C 1～C 4Alkyl or CH 2CH=CH 2Or R 7OR 8Or R 9OR 10OH or R 11OCOR 12Or R 13COOR 14Or
Figure G2009101566400D00021
Or R 16COOR 17OR 18Or C 1～C 4A hydrogen in the alkyl is replaced by OH, CN or benzene; R 7, R 8, R 9, R 10, R 11, R 12, R 13, R 15, R 16, R 17, R 18Independent separately is C 1～C 4Alkyl;
2%～35% dye monomer B as the formula (2):
Figure G2009101566400D00022
X 5Be H or NO 2Or halogen or OR 21Or SO 2R 22R 21, R 22Independent separately is C 1～C 4Alkyl;
X 6Be H or C 1～C 4Alkyl or OR 23Or NHCOR 24R 23, R 24Independent separately is C 1～C 4Alkyl;
R 19, R 20Independent separately is C 1～C 4Alkyl or C 1～C 4Alcoxyl alkyloyloxyethyl alkyl (as CH 2CH 2OCOOCH 3) or C 1～C 4Alkanoic acid alkane ester or C 1～C 4Alkyl in a hydrogen replaced by CN, OH, benzene, oxyalkyl, alkyloyl or benzoyl group;
8%～50% dye monomer C as the formula (3):
Figure G2009101566400D00023
X 7, X 8Independent separately is H or halogen;
X 9Be H or C 1～C 4Alkyl or halogen;
R 25, R 26Independent separately is H or C 1～C 4Alkyl or R 27OCOR 28Or
Figure G2009101566400D00024
Or
Figure G2009101566400D00025
Or
Figure G2009101566400D00026
Or R 33OCOOR 34Or CH 2CH=CH 2Or R 35OR 36CN or C 1～C 4Alkanoic acid alkane ester or C 1～C 4Alkyl in a hydrogen replaced by OH, CN or benzene; R 27, R 28, R 29, R 30, R 31, R 32, R 33, R 34, R 35, R 36Independent separately is C 1～C 4Alkyl;
1%～10% dye monomer D as the formula (4):
Figure G2009101566400D00031
X 10, X 11, X 12, X 13, X 14Independent separately is H or NO 2Or halogen or
Figure G2009101566400D00032
Or OR 39Or COOR 40OR 41OR 42Or Ph-R 43COO-or COOR 44COOR 45Or COOR 46-Ph; R 39, R 40, R 41, R 42, R 43, R 44, R 45, R 46Independent separately is C 1～C 4Alkyl; R 37Be C 1～C 4Alkyl;
R 38Be H or C 1～C 4Alkyl or C 1～C 4Alkyl in a hydrogen replaced by oxyalkyl.
Described dye monomer A is preferably suc as formula a kind of dye monomer shown in (1-1)～(1-24) or the mixture of multiple dye monomer:
Figure G2009101566400D00041
Figure G2009101566400D00061
Figure G2009101566400D00071
Dye monomer B is preferably suc as formula a kind of dye monomer shown in (2-1)～(2-11) or the mixture of multiple dye monomer:
Figure G2009101566400D00072
Figure G2009101566400D00081
Dye monomer C is preferably suc as formula a kind of dye monomer shown in (3-1)～(3-18) or the mixture of multiple dye monomer:
Figure G2009101566400D00092
Figure G2009101566400D00101
Figure G2009101566400D00111
Dye monomer D is preferably suc as formula a kind of dye monomer shown in (4-1)～(4-13) or the mixture of multiple dye monomer:
Figure G2009101566400D00112
Figure G2009101566400D00131
Dyestuff of the present invention needs to add auxiliary agent usually when composite.Described auxiliary agent is dispersed dye dispersion agent, diffusant and tensio-active agents thereof etc. commonly used when composite, preferably includes one of following or its mixture: naphthalene sulfonic acidformaldehyde condensation product, sulfonated lignin, alkyl naphthalene sulfonic acid formaldehyde condensation products.As condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF), naphthalene sulfonic acidformaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic formaldehyde condensation compound (dispersing agent CNF), sodium lignosulfonate (xylogen 85A, 83A) etc.Usually, auxiliary agent is 0.7～4.5 with the ratio of former dyestuff weight: 1.
Environmental-friendly disperse dye composition of the present invention can be used by the below method and prepare:
After dye monomer mixed by said ratio, in the presence of auxiliary agent, water or other tensio-active agent, carry out corpusculed with pulverizers such as sand mill or shredders; Also the former dyestuff of dye monomer carries out corpusculed with pulverizers such as sand mill or shredders respectively in the presence of auxiliary agent, water or other tensio-active agent, mixes by said ratio again.
Described dye monomer A, dye monomer B, dye monomer C, dye monomer D can adopt the commercially available prod.
It is aqueous that environmental-friendly disperse dye composition of the present invention grinds the back with sand mill or shredder, is powdery, particulate state after the spraying drying.Environmental-friendly disperse dye composition of the present invention can be according to dye monomer A, B, C, D and the adjustment of auxiliary agent ratio are deceived, blue, ash, coloured light such as palm fibre, the gained dye composite is the environmental protection dyestuff, meet environmental protection and the ecological requirement of the Oeko-Tex standard of the European Community 100, and the subject range of pH value is broad when dyeing, depth is good, opacifying property strong, lifting force, dye yield, level-dyeing property, every fastness is all good, can improve dye utilization rate greatly, reduce dyeing waste, and be that every performance approaches one of orange disperse dye composition of piecing together the black blue series of making of 76# most when at present each grade Polyester Fibers being dyeed.
Embodiment
The invention will be further described below in conjunction with embodiment and Comparative Examples, but protection scope of the present invention is not limited to this.
Embodiment 1～48
According to data shown in the table 1, after dye monomer A, dye monomer B, dye monomer C, dye monomer D and dispersion agent condensation compound of methyl naphthalene sulfonic acid and formaldehyde (MF), diffusant benzyl sulfonic formaldehyde condensation compound (CNF), diffusant naphthalene sulfonic acidformaldehyde condensation product (NNO), sodium lignosulfonate and other tensio-active agent added water and piece together to mix, grind dispersion with sand milling, carry out spraying drying then.
The EX-SF DISPERSE BLUE EX-SF 300 291:2 that dye monomer shown in its Chinese style (1-1) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the EX-SF DISPERSE BLUE EX-SF 300 291:1 that dye monomer shown in the formula (1-2) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the EX-SF DISPERSE BLUE EX-SF 300 291 that dye monomer shown in the formula (1-3) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the EX-SF DISPERSE BLUE EX-SF 300 291 that dye monomer shown in the formula (1-4) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the EX-SF DISPERSE BLUE EX-SF 300 291:4 that dye monomer shown in the formula (1-5) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the 63 DISPERSE Violet 63 93# that dye monomer shown in the formula (1-6) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the 63 DISPERSE Violet 63 93:1# that dye monomer shown in the formula (1-7) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the Disperse Blue-79 # that dye monomer shown in the formula (1-8) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the dye monomer shown in the formula (1-9) can select the EX-SF DISPERSE BLUE EX-SF 300 183:1# of Zhejiang Province Runtu intercalated Co., Ltd's production etc. for use.
The Red-1 200 45# that dye monomer shown in its Chinese style (2-1) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the Red-1 200 79# that dye monomer shown in the formula (2-2) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the Disperse Red 58# that dye monomer shown in the formula (2-3) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the Red-1 200 56# that dye monomer shown in the formula (2-4) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the dye monomer shown in the formula (2-5) can select the Red-1 200 77 of Zhejiang Province Runtu intercalated Co., Ltd's production etc. for use.
The DISPERSE ORANGE 30 200 278# that dye monomer shown in its Chinese style (3-1) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE ORANGE 30 200 288# that dye monomer shown in the formula (3-2) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE ORANGE 30 200 298# that dye monomer shown in the formula (3-3) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE ORANGE 30 200 279# that dye monomer shown in the formula (3-4) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE ORANGE 30 200 30:2 that dye monomer shown in the formula (3-5) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE ORANGE 30 200 30# that dye monomer shown in the formula (3-6) can select for use Zhejiang Province Runtu intercalated Co., Ltd to produce, the dye monomer shown in the formula (3-7) can select the DISPERSE ORANGE 30 200 61# of Zhejiang Province Runtu intercalated Co., Ltd's production etc. for use.
The DISPERSE YELLOW 114# that dye monomer shown in its Chinese style (4-1) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE YELLOW 119# that dye monomer shown in the formula (4-2) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE Yellow 211 # that dye monomer shown in the formula (4-3) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce, the DISPERSE YELLOW 241# that dye monomer shown in the formula (4-4) can adopt Zhejiang Province Runtu intercalated Co., Ltd to produce, the dye monomer shown in the formula (4-5) can adopt the DISPERSE YELLOW 126# of Zhejiang Province Runtu intercalated Co., Ltd's production etc.
Table 1:
Figure G2009101566400D00151
Figure G2009101566400D00161
Figure G2009101566400D00171
Figure G2009101566400D00181
Comparative Examples is DISPERSE ORANGE 30 200 288#10g, EX-SF DISPERSE BLUE EX-SF 300 291:350g and the composite dye composite of 63 DISPERSE Violet 63 93:140g that adopts Zhejiang Province Runtu intercalated Co., Ltd to produce.
With the dispersed dye that the foregoing description makes, auxiliary agent, the dye composite that water makes after mixing and the disperse dye composition of Comparative Examples carry out performance test, and testing method is as follows:
Respectively get the dispersed dye of 1.0 gram embodiment 1～48, water is mixed with the dispersed dye suspension that concentration is 1g/500ml respectively, gets 10ml, 50ml, 80ml and 90ml, 50ml, the water of 20ml mixes, dye abundant pH to 5 with the acetic acid adjusting, be warmed up to 60 ℃ then, put into the 2g trevira simultaneously respectively and carry out high-temperature pressure dyeing, in 35 minutes, be warmed up to 130 ℃, be incubated 30 minutes, sampling when being cooled to 80 ℃.
Observe cloth specimen coloured light and adopt GB/T2397-2003, GB/T3921-1997, GB/T3920-1997, GB/T5178-1997 measure its dyefastness.Measurement result sees Table 2.
Embodiment Lifting force Washing fastness Crock fastness Sublimation fastness (180 ℃)
Embodiment 1 ??A ??4-5 ??5 ??4-5
Embodiment 2 ??A ??4-5 ??5 ??4-5
Embodiment 3 ??A ??4-5 ??5 ??4-5
Embodiment 4 ??A ??4-5 ??5 ??4-5
Embodiment 5 ??A ??4-5 ??5 ??4-5
Embodiment 6 ??A ??4-5 ??5 ??4
Embodiment 7 ??A ??4-5 ??5 ??4
Embodiment 8 ??A ??4-5 ??5 ??4-5
Embodiment Lifting force Washing fastness Crock fastness Sublimation fastness (180 ℃)
Embodiment 9 ??A ??4-5 ??5 ??4-5
Embodiment 10 ??A ??4-5 ??5 ??4-5
Embodiment 11 ??A ??4-5 ??5 ??4-5
Embodiment 12 ??A ??4-5 ??5 ??4-5
Embodiment 13 ??A ??4-5 ??5 ??4-5
Embodiment 14 ??A ??4-5 ??5 ??4-5
Embodiment 15 ??A ??4-5 ??5 ??4-5
Embodiment 16 ??A ??4-5 ??5 ??4-5
Embodiment 17 ??A ??4-5 ??5 ??4
Embodiment 18 ??A ??4-5 ??5 ??4
Embodiment 19 ??A ??4-5 ??5 ??4
Embodiment 20 ??A ??4-5 ??5 ??4-5
Embodiment 21 ??A ??4-5 ??5 ??4-5
Embodiment 22 ??A ??4-5 ??5 ??4-5
Embodiment 23 ??A ??4-5 ??5 ??4-5
Embodiment 24 ??A ??4-5 ??5 ??4-5
Embodiment 25 ??A ??4-5 ??5 ??4-5
Embodiment 26 ??A ??4-5 ??5 ??4-5
Embodiment 27 ??A ??4-5 ??5 ??4-5
Embodiment 28 ??A ??4-5 ??5 ??4-5
Embodiment 29 ??A ??4-5 ??5 ??4
Embodiment 30 ??A ??4-5 ??5 ??4-5
Embodiment Lifting force Washing fastness Crock fastness Sublimation fastness (180 ℃)
Embodiment 31 ??A ??4-5 ??5 ??4-5
Embodiment 32 ??A ??4-5 ??5 ??4-5
Embodiment 33 ??A ??4-5 ??5 ??4-5
Embodiment 34 ??A ??4-5 ??5 ??4-5
Embodiment 35 ??A ??4-5 ??5 ??4-5
Embodiment 36 ??A ??4-5 ??5 ??4-5
Embodiment 37 ??A ??4-5 ??5 ??4-5
Embodiment 38 ??A ??4-5 ??5 ??4-5
Embodiment 39 ??A ??4-5 ??5 ??4-5
Embodiment 40 ??A ??4-5 ??5 ??4-5
Embodiment 41 ??A ??4-5 ??5 ??4-5
Embodiment 42 ??A ??4-5 ??5 ??4-5
Embodiment 43 ??A ??4-5 ??5 ??4-5
Embodiment 44 ??A ??4-5 ??5 ??4-5
Embodiment 45 ??A ??4-5 ??5 ??4-5
Embodiment 46 ??A ??4-5 ??5 ??4-5
Embodiment 47 ??A ??4-5 ??5 ??4-5
Embodiment 48 ??A ??4-5 ??5 ??4-5
Comparative Examples ??A-B ??4 ??4 ??4-5

Claims (5)

1. the disperse dye composition of an environment-friendly type, by weight percentage, mainly form by following component:
10%～75% dye monomer A as the formula (1):
Figure F2009101566400C00011
X wherein 1Be H or CN or NO 2
X 2Be H or halogen, and X 1And X 2Be not H simultaneously;
X 3Be H or C 1～C 4Alkyl or NHCOR 3Or OH; R 3Be C 1～C 4Alkyl;
X 4Be H or OH or OR 4Or R 5OR 6R 4, R 5, R 6Independent separately is C 1～C 4Alkyl;
R 1, R 2Independent separately is H or C 1～C 4Alkyl or CH 2CH=CH 2Or R 7OR 8Or R 9OR 10OH or R 11OCOR 12Or R 13COOR 14Or R 15OCO
Figure F2009101566400C00012
Or R 16COOR 17OR 18Or C 1～C 4A hydrogen in the alkyl is replaced by OH, CN or benzene; R 7, R 8, R 9, R 10, R 11, R 12, R 13, R 15, R 16, R 17, R 18Independent separately is C 1～C 4Alkyl;
2%～35% dye monomer B as the formula (2):
Figure F2009101566400C00013
X 5Be H or NO 2Or halogen or OR 21Or SO 2R 22R 21, R 22Independent separately is C 1～C 4Alkyl;
X 6Be H or C 1～C 4Alkyl or OR 23Or NHCOR 24R 23, R 24Independent separately is C 1～C 4Alkyl;
R 19, R 20Independent separately is C 1～C 4Alkyl or C 1～C 4Alcoxyl alkyloyloxyethyl alkyl (as CH 2CH 2OCOOCH 3) or C 1～C 4Alkanoic acid alkane ester or C 1～C 4Alkyl in a hydrogen replaced by CN, OH, benzene, oxyalkyl, alkyloyl or benzoyl group;
8%～50% dye monomer C as the formula (3):
Figure F2009101566400C00021
X 7, X 8Independent separately is H or halogen;
X 9Be H or C 1～C 4Alkyl or halogen;
R 25, R 26Independent separately is H or C 1～C 4Alkyl or R 27OCOR 28Or R 29OCONH
Figure F2009101566400C00022
Or R 30OCO
Figure F2009101566400C00023
Or R 31OCOR 32
Figure F2009101566400C00024
Or R 33OCOOR 34Or CH 2CH=CH 2Or R 35OR 36CN or C 1～C 4Alkanoic acid alkane ester or C 1～C 4Alkyl in a hydrogen replaced by OH, CN or benzene; R 27, R 28, R 29, R 30, R 31, R 32, R 33, R 34, R 35, R 36Independent separately is C 1～C 4Alkyl;
1%～10% dye monomer D as the formula (4):
Figure F2009101566400C00025
X 10, X 11, X 12, X 13, X 14Independent separately is H or NO 2Or halogen or
Figure F2009101566400C00026
Or OR 39Or COOR 40OR 41OR 42Or Ph-R 43COO-or COOR 44COOR 45Or COOR 46-Ph;
R 39, R 40, R 41, R 42, R 43, R 44, R 45, R 46Independent separately is C 1～C 4Alkyl;
R 37Be C 1～C 4Alkyl;
R 38Be H or C 1～C 4Alkyl or C 1～C 4Alkyl in a hydrogen replaced by oxyalkyl.
2. disperse dye composition as claimed in claim 1 is characterized in that: described dye monomer A is suc as formula a kind of dye monomer shown in (1-1)～(1-24) or the mixture of multiple dye monomer:
Figure F2009101566400C00031
Figure F2009101566400C00041
Figure F2009101566400C00051
Figure F2009101566400C00061
3. disperse dye composition as claimed in claim 1 is characterized in that: described dye monomer B is suc as formula a kind of dye monomer shown in (2-1)～(2-11) or the mixture of multiple dye monomer:
Figure F2009101566400C00071
Figure F2009101566400C00081
4. disperse dye composition as claimed in claim 1 is characterized in that: described dye monomer C is suc as formula a kind of dye monomer shown in (3-1)～(3-18) or the mixture of multiple dye monomer:
Figure F2009101566400C00082
Figure F2009101566400C00091
Figure F2009101566400C00101
5. disperse dye composition as claimed in claim 1 is characterized in that: described dye monomer D is suc as formula a kind of dye monomer shown in (4-1)～(4-13) or the mixture of multiple dye monomer:
Figure F2009101566400C00111
Figure F2009101566400C00121
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